Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C233/00—Carboxylic acid amides
  • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
  • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
  • C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
  • C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
  • A01N37/46—N-acyl derivatives
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
  • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
  • A01N41/04—Sulfonic acids; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
  • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
  • A01N41/04—Sulfonic acids; Derivatives thereof
  • A01N41/08—Sulfonic acid halides; alpha-Hydroxy-sulfonic acids; Amino-sulfonic acids; Thiosulfonic acids; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
  • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
  • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
  • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
  • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D307/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
  • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Definitions

• the present invention relates to compounds of the formula I ##STR3## wherein R 1 and R 2 independently of one another are each C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy or halogen,
• R 3 is hydrogen, C 1 -C 3 -alkyl or halogen
• R 4 is hydrogen or methyl, the total number of carbon atoms in R 1 , R 2 , R 3 and R 4 not exceeding 6,
• R 5 is C 3 -C 8 -alkyl, C 2 -C 6 -alkenyl or C 3 -C 6 -alkynyl both unsubstituted or substituted by halogen, or it is C 3 -C 7 -cycloalkyl unsubstituted or substituted by halogen or C 1 -C 3 -alkyl, or it is C 6 -C 10 -aryl unsubstituted or substituted by halogen, cyano, nitro, C 1 -C 3 -alkyl, C 1 -C 3 -alkoxy or C 1 -C 2 -halogenoalkyl,
• R 6 is 2-furyl or 2-tetrahydrofuryl both unsubstituted or substituted by halogen, or R 6 is ⁇ -(C 1 -C 4 )-alkoxyethyl, or the group CH 2 Z, where Z is one of the groups (a) --X--R 7 , (b) --NH--N(R 8 )(R 9 ), (c) --OSO 2 R 10 and (d) ##STR4## wherein X is oxygen or sulfur, R 7 is C 1 -C 6 -alkyl which is unsubstituted or substituted by C 1 -C 2 -alkoxy, or it is C 3 -C 4 -alkenyl or C 3 -C 4 -alkynyl, R 8 is hydrogen or C 1 -C 3 -alkyl, R 9 is C 1 -C 3 -alkyl, or phenyl which is unsubstituted or substituted by halogen or by methyl, R 10 is
• alkyl or by alkyl part of another substitutent are meant, depending on the given number of C atoms, the following groups: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, and also isomers thereof, for example iso-propyl, iso-butyl, sec-butyl, tert-butyl, iso-pentyl, and so forth.
• Alkenyl is for example allyl, 2-butenyl, 3-pentenyl, etc.
• Alkynyl denotes in particular propargyl.
• C 3 -C 7 -cycloalkyl are meant cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl.
• aryl is meant in particular phenyl and naphthyl.
• Halogen is fluorine, chlorine, bromine or iodine.
• the compounds of the formula I can be produced by a whole series of methods, such as by those described in the following.
• R 1 to R 11 and X have the meanings given under the formula I
• "Hal" denotes halogen, preferably chlorine or bromine
• M is hydrogen or a metal cation, preferably an alkali metal cation or alkaline-earth metal cation.
• a reactive derivative of a compound of the formula III for example the acid halide, acid anhydride or the ester.
• Method A may be modified by starting with compound II wherein R 5 represents hydrogen which method results in compound XVI hereunder, with subsequent esterification by method G.
• acid-binding agents and/or condensation agents are advantageous. Suitable as such are for example: tertiary amines such as trialkylamines (for example triethylamine), pyridine or pyridine bases, or inorganic bases, such as the oxides, hydroxides, hydrogen carbonates, carbonates or hydrides of alkali metals and alkaline-earth metals, and also sodium acetate.
• tertiary amines such as trialkylamines (for example triethylamine), pyridine or pyridine bases, or inorganic bases, such as the oxides, hydroxides, hydrogen carbonates, carbonates or hydrides of alkali metals and alkaline-earth metals, and also sodium acetate.
• the starting product II can moreover serve as acid-binding agent, and should be used in excess.
• the production process A can also be performed without an acid-binding agent. In some cases the passing through of nitrogen to expel the hydrogen halide formed is advisable. In other cases, an addition of dimethylformamide as reaction catalyst is very advantageous.
• a salt, especially an alkali metal salt, of the compound of the formula IV can be carried out, as described under A, in the presence of an acid-binding agent.
• R 6 has a meaning other than --CH 2 NH--N(R 8 )(R 9 ): ##STR7##
• the compound of the formula VII is firstly converted with butyl-lithium or sodium hydride into the corresponding alkali metal salt, or alternatively the process is performed in the presence of an acid-binding agent, analogously to process A, preferably with the addition of catalytic amounts of alkali iodide.
• R 6 is --CH 2 XR 7 , --CH 2 O(CO)R 11 or --CH 2 NH--N(R 8 )(R 9 ): ##STR8##
• M is hydrogen
• a salt-forming agent for example the oxide, hydroxide or hydride of an alkali metal or alkaline-earth metal.
• the final product is obtained as hydrogen halide.
• mild bases it is possible to obtain at room temperature or at slightly elevated temperature the free hydrazino compound. Suitable for this are for example alkali carbonates.
• esterfication catalyst for example mineral acids, chlorosulfonic acid, toluenesulfonic acid, acid chlorides such as thionyl chloride, acetyl chloride, phosphorus oxychloride, oxalyl chloride, boron trifluoride etherate, and so forth. It is also possible to carry out the reaction with an excess of HOR 5 .
• the azeotropic esterification method is advantageous in many cases.
• This reaction is catalytically influenced by acids and bases. In order to displace the equilibrium as far as possible in the desired direction, the reaction is performed with an excess of HOR 5 .
• the meanings of R' and R 5 are different.
• R' is preferably lower alkyl, such as methyl or ethyl.
• Me denotes an alkali metal, alkaline-earth metal, lead or silver atom
• Hal' is halogen, preferably chlorine, bromine or iodine.
• R" is here lower alkyl, preferably methyl.
• solvents which are inert to the reactants.
• solvents are: aliphatic hydrocarbons, such as benzene, toluene, xylenes or petroleum ether; halogenated hydrocarbons, such as chlorobenzene, methylene chloride, ethylene chloride or chloroform; ethers and ethereal compounds, such as dialkyl ether, dioxane and tetrahydrofuran; nitriles, such as acetonitrile; N,N-dialkylated amides, such as dimethylformamide; dimethyl sulfoxide, ketones, such as methyl ethyl ketone; and mixtures of solvents of this type.
• the compounds of the formula I have, in a position adjacent to COOR 5 , an asymmetrical carbon atom in the side chain, and can be split in the customary manner into optical antipodes (fractional crystallisation or column chromatography either with compounds of the formula I or with the intermediate products, and further reaction of the resolved antipodes).
• the antipodes I have a varying microbicidal action.
• asymmetrical carbon atoms can be present in the molecule, depending on substitution.
• Suitable carriers and additives can be solid or liquid and they correspond to the substances common in formulation practice, such as natural or regenerated mineral substances, solvents, dispersing agents, wetting agents, adhesives, thickeners, binders and/or fertilisers. Dispersing agents and wetting agents belong to the surface-active additives.
• the content of active substance in commercial compositions is between 0.1 and 90%.
• the compounds of the formula I can be in the following forms for application (the weight-percentage figures in brackets signify advantageous amounts of active substance):
• water-dispersible concentrates of active substance wettable powders and pastes (25 to 90% in the commercial packing, 0.01 to 15% in ready-for-use solutions); emulsion concentrates and solution concentrates (10 to 50%; 0.01 to 15% in ready-for-use solutions);
• compositions of this type likewise form subject matter of the present invention.
• Cultivated plants within the scope of the present invention are for example: cereals, maize, rice, vegetables, sugar beet, soya bean, groundnuts, fruit trees or ornamental plants, especially however grape vines, hops, cucurbitaceae (cucumbers, pumpkins, melons), solanaceae, such as potatoes, tobacco and tomatoes, and also bananas, cocoa and natural rubber plants.
• Fungi occurring on plants or on parts of plants (fruit, blossom, foliage, stalks, tubers or roots) of the said crops and of related cultivated crops can be inhibited or destroyed with the active substances of the formula I, and also parts of plants subsequently growing remain preserved from such fungi.
• the active substances are effective against the phytopathogenic fungi belonging to the following classes: Ascomycetes (for example Erysiphaceae, Sclerotinia, Helminthosporium); Basidiomycetes, such as in particular rust fungi, Rhizoctonia; fungi imperfecti (for example Moniliales, Piricularia); and especially against the Oomycetes belonging to the Phycomycetes class, such as Phytophthora, Peronospora, Pseudoperonospora, Pythium or Plasmopara.
• the compounds of the formula I have a systemic action. They can also be used as dressing agents for the treatment of seed (fruits, tubers, grain, etc.) and plant cuttings to protect them from fungus infections, and also against phytopathogenic fungi occurring in the soil.
• the invention hence relates also to the use of the compounds of the formula I for controlling phytopathogenic microorganisms.
• R 1 is C 1 -C 2 -alkyl or C 1 -C 2 -alkoxy
• R 2 is CH 3 , --OCH 3 or halogen
• R 3 is hydrogen, CH 3 or halogen
• R 4 is hydrogen or CH 3 ,
• R 5 is C 3 -C 6 -alkyl or C 2 -C 4 -alkenyl, C 3 -C 4 -alkynyl or C 3 -C 7 -cycloalkyl,
• R 6 is 2-furyl, 2-tetrahydrofuryl, ⁇ -(C 1 -C 2 -alkoxy)-ethyl or CH 2 Z, the meaning of Z being --OR 7 , --SR 7 , --NH--N(R 8 )(R 9 ) or --OSO 2 R 10 , wherein R 7 is C 1 -C 4 -alkyl which is unsubstituted or substituted by C 1 -C 2 -alkoxy, or it is C 3 -C 4 -alkenyl or C 3 -C 4 -alkynyl, R 8 and R 9 independently of one another are each C 1 -C 3 -alkyl, and R 10 is C 1 -C 2 -alkyl or monomethylamine.
• R 1 is CH 3 or OCH 3 ,
• R 2 is CH 3 or chlorine
• R 3 is hydrogen
• R 4 is hydrogen
• R 5 is C 3 -C 4 -alkyl, C 3 -alkenyl or C 3 -alkynyl,
• R 6 is 2-furyl, 2-tetrahydrofuryl, CH 2 CH 2 OCH 3 or CH 2 Z, the meaning of Z being --OR 7 , --NH--N(R 8 )(R 9 ) or --OSO 2 R 10 , wherein R 7 is C 1 -C 3 -alkyl, R 8 and R 9 independently of one another are each C 1 -C 2 -alkyl, and R 10 is C 1 -C 2 -alkyl or monomethylamine.
• the active substances are intimately mixed in suitable mixers with the additives, and the mixture is then ground in the appropriate mills and rollers. There are obtained wettable powders which have excellent wetting and suspension properties, and which can be diluted with water to give suspensions of the desired concentration, and these are particularly suitable for leaf application.
• Emulsifiable concentrate is a liquid crystal
• Emulsions of the desired concentration can be prepared from these concentrates by dilution with water, and they are particularly suitable for leaf application.
• Tomato plants after three-weeks' cultivation were sprayed with a spray liquor prepared from wettable powder of the active substance (0.06% of active substance).
• the treated plants were infested after 24 hours with a suspension of sporangia of the fungus.
• An assessment of the fungus infection was made after incubation of the infested plants during 5 days at 90-100% relative humidity at 20° C.
• Tomato plants were infested, after a cultivation period of three weeks, with a suspension of sporangia of the fungus. After an incubation time of 22 hours in a moist chamber at 20° C. with 90-100% relative humidity, the infested plants were dried, and then sprayed with a spray liquor prepared from wettable powder of the active substance (0.06% of active substance). After drying of the applied coating, the treated plants were returned to the moist chamber. The assessment of fungus infection was carried out 5 days after infestation.
• a spray liquor prepared from wettable powder of the active substance (0.006% of active substance, relative to the volume of soil) was applied to the soil in which tomato plants had been cultivated for 3 weeks. Care was taken to ensure that the spray liquor did not come into contact with the parts of the plants above the soil. After 48 hours, the treated plants were infested with a suspension of sporangia of the fungus. An assessment of fungus infection was made after incubation of the infested plants during 5 days at 20° C. with 90-100% relative humidity.
• Grape-vine cuttings in the 4-5-leaf stage were sprayed with a spray liquor prepared from wettable powder of the active substance (0.06% of active substance). After 24 hours, the treated plants were infested with a suspension of sporangia of the fungus. The extent of fungus infection was assessed after incubation during 6 days at 20° C. with 95-100% relative humidity.
• the fungus was cultivated on a carrot-chips nutrient solution, and applied to a soil/sand mixture.
• the soil infested in this manner was placed into flower pots, and sown with sugar-beet seeds.
• the test preparations formulated as wettable powder, were poured as aqueous suspensions over the soil (20 ppm of active substance, relative to the volume of soil).
• the pots were subsequently left for 2-3 weeks in a greenhouse at about 20° C.
• the soil was continuously maintained uniformly moist by light spraying.
• the fungus was cultivated on a carrot-chips nutrient solution, and applied to a soil/sand mixture.
• the soil infested in this manner was placed into soil trays, and sown with sugar-beet seeds which had been dressed with the test preparations formulated as dressing powder (0.06% of active substance).
• the sown trays were left for 2-3 weeks in a greenhouse at about 20° C.
• the soil was continuously maintained uniformly moist by light spraying. In the final evaluation, the sprouting of the plants was assessed.
• Barley plants about 8 cm high were sprayed with a liquor prepared from wettable powder of the active substance No. 64 (containing 0.006% of active substance). After 4 hours, the treated plants were dusted with conidiospores of the fungus. The infested barley plants were kept in a greenhouse at about 22° C. Whereas the control plants after 10 days were displaying clear symptoms of disease, the plants treated with the active substance No. 64 were free from infection.

Landscapes

• Life Sciences & Earth Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Plant Pathology (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Pest Control & Pesticides (AREA)
• Agronomy & Crop Science (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Furan Compounds (AREA)

Applications Claiming Priority (2)

Related Parent Applications (1)

Publications (1)

Family

ID=4370274

Family Applications (1)

Country Status (15)

Cited By (3)

Families Citing this family (2)

Citations (7)

Family Cites Families (10)

• 1978
  • 1978-10-27 CH CH1111978A patent/CH637368A5/de not_active IP Right Cessation
• 1979
  • 1979-10-23 NL NL7907786A patent/NL7907786A/nl not_active Application Discontinuation
  • 1979-10-23 GB GB7936727A patent/GB2037746B/en not_active Expired
  • 1979-10-24 DE DE19792943019 patent/DE2943019A1/de active Granted
  • 1979-10-24 FR FR7926387A patent/FR2439768A1/fr active Granted
  • 1979-10-25 CA CA000338475A patent/CA1151192A/en not_active Expired
  • 1979-10-25 AT AT0694179A patent/AT365039B/de not_active IP Right Cessation
  • 1979-10-26 IT IT26835/79A patent/IT1124679B/it active
  • 1979-10-26 AU AU52224/79A patent/AU533580B2/en not_active Ceased
  • 1979-10-26 IL IL58569A patent/IL58569A/xx unknown
  • 1979-10-26 KR KR7903736A patent/KR840000846B1/ko active
  • 1979-10-26 BE BE0/197837A patent/BE879661A/fr not_active IP Right Cessation
  • 1979-10-26 ZA ZA00795727A patent/ZA795727B/xx unknown
  • 1979-10-27 JP JP13919879A patent/JPS5559148A/ja active Pending
• 1981
  • 1981-01-05 US US06/222,406 patent/US4330556A/en not_active Expired - Fee Related

Patent Citations (7)

Non-Patent Citations (3)

Also Published As

Similar Documents

Legal Events